Sodium Bicarbonate → 4-Hydroxy-7-[2-[[3-[[2-(2-phenylethoxy)ethyl]sulfonyl]propyl]amino]ethyl]-2(3H)-benzothiazolone
Reaction equation
Cl.[OH:2][C:3]1[C:8]2[NH:9][C:10](=[O:12])[S:11][C:7]=2[C:6]([CH2:13][CH2:14][NH:15][CH2:16][CH2:17][CH2:18][S:19]([CH2:22][CH2:23][O:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:21])=[O:20])=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+]>>[OH:2][C:3]1[C:8]2[NH:9][C:10](=[O:12])[S:11][C:7]=2[C:6]([CH2:13][CH2:14][NH:15][CH2:16][CH2:17][CH2:18][S:19]([CH2:22][CH2:23][O:24][CH2:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)(=[O:21])=[O:20])=[CH:5][CH:4]=1Participants
3
Procedure
An aqueous solution (500 ml) of the title compound from Example 20 (4.9 g) was mixed with an excess of aqueous sodium hydrogen carbonate. The free base was extracted with chloroform and the combined extracts were washed with water and dried (MgSO4), filtered and the chloroform removed under reduced pressure to yield the subtitled compound as an off-white solid (4.22 g, 91%).
Workup
- extractionThe free base was extracted with chloroform
- wash